US11447505B1ActiveUtility
Pyrrolo[2,3-b]pyridine compounds and their use in the treatment of cancer
Est. expiryAug 18, 2037(~11.1 yrs left)· nominal 20-yr term from priority
Inventors:Angelo PuglieseStuart FrancisDuncan Robert McarthurMairi SimeJustin Fairfield BowerSimone Belshaw
C07D 487/10C07D 471/04C07D 487/04C07D 471/10C07D 519/00A61P 35/04C07F 7/0812
71
PatentIndex Score
2
Cited by
6
References
15
Claims
Abstract
The present application relates to a compound of Formula I, or a salt, hydrate or solvate thereof, as defined herein. The present compounds are found to have pharmacological effects, particularly at MRCK. Further provided are pharmaceutical compositions comprising said compounds. The present invention also relates to the use of these compounds as therapeutic agents, in particular, for the treatment and/or prevention of proliferative diseases, such as cancer.
Claims
exact text as granted — not AI-modifiedThe invention claimed is:
1. A compound of Formula I, or a salt, hydrate or solvate thereof;
wherein,
R 4 is a group of formula II,
R 3 is selected from 5-15 membered heteroaryl, where said 5-15 membered heteroaryl is optionally substituted by one or more R b ;
each R b is selected from hydrogen, hydroxyl, halogen, CN, C 1-6 alkyl and O—C 1-6 alkyl; wherein said C 1-6 alkyl is optionally substituted with one or more groups selected from hydroxyl, halogen, ═O, NR c R d , C 1-6 alkyl, O—C 1-6 alkyl, and phenyl;
each R c is independently selected from hydrogen and C 1-6 alkyl;
each R d is independently selected from hydrogen, CN, C 1-6 haloalkyl, O—C 1-6 haloalkyl, 3-7 membered heterocycloalkyl, 5-6 membered heteroaryl, C 3-6 cycloalkyl, C 1-6 alkyl, O—C 1-6 alkyl and phenyl, wherein said C 1-6 alkyl, phenyl, 5-6 membered heteroaryl, 3-7 membered heterocycloalkyl and C 3-6 cycloalkyl are optionally substituted with one or more groups selected from hydroxyl, halogen, CN, NH 2 , NH(C 1-6 alkyl), N(C 1-6 alkyl) 2 , C 1-6 haloalkyl, C 3-6 cycloalkyl, phenyl, 3-7 membered heterocycloalkyl, C 3-10 alkylheterocycloalkyl, C 1-6 alkyl and O—C 1-6 alkyl; or
R c and R d , when attached to the same atom, together with the atom to which they are attached form a 3-7 membered heterocycloalkyl ring optionally substituted by one or more groups selected from hydroxyl, halogen, CN, NH 2 , NH(C 1-6 alkyl), N(C 1-6 alkyl) 2 , C 1-6 haloalkyl, O—C 1-6 haloalkyl, C 3-6 cycloalkyl, phenyl, 3-7 membered heterocycloalkyl, C 1-6 alkyl and O—C 1-6 alkyl;
R 5 is selected from hydrogen, halogen, hydroxyl, NH 2 , NH(C 1-6 alkyl), N(C 1-6 alkyl) 2 , C 1-6 alkyl, O—C 1-6 alkyl, C 1-6 haloalkyl, O—C 1-6 haloalkyl, C 3-6 cycloalkyl, phenyl and CN;
R 9 and R 10 are independently selected from hydroxyl, C 1-6 alkyl, O—C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 haloalkoxy, NH 2 , NH(C 1-6 alkyl), N(C 1-6 alkyl) 2 , NR c R d , NR c C(═O)R d , C(O)NR c R d , phenyl, and 3-7 membered heterocycloalkyl, where said C 1-6 alkyl, phenyl and 3-7 membered heterocycloalkyl are optionally substituted with one or more groups selected from halogen, hydroxyl, CN, NH 2 , NH(C 1-6 alkyl), N(C 1-6 alkyl) 2 , C 1-6 alkyl, O—C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 haloalkoxy, C 3-6 cycloalkyl and phenyl; or
R 9 and R 10 together with the carbon atom to which they are attached form a 4-6 membered heterocycloalkyl ring comprising at least one heteroatom selected from O, N and S, where said heterocycloalkyl ring is optionally substituted with one or more R m ;
R m is selected from hydroxyl, halogen, CN, C 1-6 alkyl, C 3-6 cycloalkyl, C 1-6 haloalkyl, and OR a ; where R a is defined above; and
n is a number selected from 0 and 1.
2. The compound according to claim 1 , or a salt, hydrate or solvate thereof, wherein R 4 is selected from
where each is optionally substituted on a carbon atom by one or more R i , wherein R j is selected from halogen, C 1-6 alkyl, hydroxyl and O—C 1-6 alkyl with the proviso that R j is selected from halogen and C 1-6 alkyl when bonded to a carbon adjacent to N.
3. The compound according to claim 1 , or a salt, hydrate or solvate thereof, wherein R 9 and R 10 are independently selected from hydroxyl, C 1-6 alkyl, NH 2 , NH(C 1-6 alkyl), N(C 1-6 alkyl) 2 , NR c R d , NR c C(═O)R d , C(O)NR c R d , phenyl, and 3-7 membered heterocycloalkyl, where said C 1-6 alkyl, phenyl and 3-7 membered heterocycloalkyl are optionally substituted with one or more groups selected from halogen, hydroxyl, CN, NH 2 , NH(C 1-6 alkyl), N(C 1-6 alkyl) 2 , C 1-6 alkyl, O—C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 haloalkoxy, C 3-6 cycloalkyl and phenyl; or
R 9 and R 10 together with the carbon atom to which they are attached form a 4-6 membered heterocycloalkyl ring comprising at least one heteroatom selected from O, N and S, where said heterocycloalkyl ring is optionally substituted with one or more R m .
4. The compound according to any claim 1 , or a salt, hydrate or solvate thereof, wherein R m is selected from C 1-3 alkyl.
5. The compound according to claim 1 , or a salt, hydrate or solvate thereof, wherein R 3 is selected from 5-6 membered heteroaryl, where said 5-6 membered heteroaryl is optionally substituted by one or more R b .
6. The compound according to claim 1 , or a salt, hydrate or solvate thereof, wherein R 3 is a 6 membered heteroaryl optionally substituted by one or more R b .
7. The compound according to claim 1 , or a salt, hydrate or solvate thereof, wherein R 3 is
optionally substituted by one or two R b groups.
8. The compound according to claim 1 , or a salt, hydrate or solvate thereof, wherein R b is selected from hydrogen and C 1-3 alkyl.
9. The compound according to claim 1 , or a salt, hydrate or solvate thereof, wherein R 5 is selected from hydrogen, halogen, hydroxyl, C 1-6 alkyl, O—C 1-6 alkyl, C 1-6 haloalkyl, O—C 1-6 haloalkyl, C 3-6 cycloalkyl, phenyl and CN.
10. The compound according to claim 1 , or a salt, hydrate or solvate thereof, of sub-formula Ic′:
wherein
ring A is a heteroaryl group selected from a pyrimidine, thiazole, thiadiazole, isothiazole, pyridazine, pyridine and pyrazine;
m is a number selected from 0, 1 and 2; and
n, R 9 and R 10 are as defined in claim 1 .
11. The compound according to claim 10 , or a salt, hydrate or solvate thereof, wherein R 9 and R 10 together with the carbon atom to which they are attached form a 5-6 membered heterocycloalkyl ring comprising one nitrogen atom, where said heterocycloalkyl ring is optionally substituted with one or more R m as defined in claim 1 .
12. The compound according to claim 1 , or a salt, hydrate or solvate thereof, selected from:
E114
4-[4-(1,8-diazaspiro[5.5]undecan-8-yl)-1H-pyrrolo[2,3-b]pyridin-3-
yl]isothiazole
E115
3-[4-[(6R)-1,8-diazaspiro[5.5]undecan-8-yl]-1H-pyrrolo[2,3-
b]pyridin-3-yl]-1,2,4-thiadiazole
E116
3-[4-[(6S)-1,8-diazaspiro[5.5]undecan-8-yl]-1H-pyrrolo[2,3-
b]pyridin-3-yl]-1,2,4-thiadiazole
E117
(6S)-8-(3-pyrimidin-4-yl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1,8-
diazaspiro[5.5]undecane
E118
(6R)-8-(3-pyrimidin-4-yl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1,8-
diazaspiro[5.5]undecane
E119
3-[4-[(6R)-1,8-diazaspiro[5.5]undecan-8-yl]-1H-pyrrolo[2,3-
b]pyridin-3-yl]isothiazole
E120
3-[4-[(6S)-1,8-diazaspiro[5.5]undecan-8-yl]-1H-pyrrolo[2,3-
b]pyridin-3-yl]isothiazole
E121
3-[4-(1,8-diazaspiro[5.5]undecan-8-yl)-1H-pyrrolo[2,3-b]pyridin-
3-yl]isothiazole
E122
(6S)-8-(3-pyrimidin-5-yl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1,8-
diazaspiro[5.5]undecane
E123
4-[(5R)-1,7-diazaspiro[4.4]nonan-7-yl]-3-pyrimidin-5-yl-1H-
pyrrolo[2,3-b]pyridine
E124
4-[(5S)-1,7-diazaspiro[4.4]nonan-7-yl]-3-pyrimidin-5-yl-1H-
pyrrolo[2,3-b]pyridine
E125
(5R)-2-(3-pyrimidin-5-yl-1H-pyrrolo[2,3-b]pyridin-4-yl)-2,6-
diazaspiro[4.5]decane
E126
(5S)-2-(3-pyrimidin-5-yl-1H-pyrrolo[2,3-b]pyridin-4-yl)-2,6-
diazaspiro[4.5]decane
E127
(5R)-2-(3-pyrimidin-4-yl-1H-pyrrolo[2,3-b]pyridin-4-yl)-2,6-
diazaspiro[4.5]decane
E128
(5S)-2-(3-pyrimidin-4-yl-1H-pyrrolo[2,3-b]pyridin-4-yl)-2,6-
diazaspiro[4.5]decane
E129
3-[4-(2,6-diazaspiro[4.5]decan-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-
yl]-1,2,4-thiadiazole
E130
2-[4-[(5R)-2,6-diazaspiro[4.5]decan-2-yl]-1H-pyrrolo[2,3-
b]pyridin-3-yl]-5-methyl-thiazole
E131
2-[4-[(5S)-2,6-diazaspiro[4.5]decan-2-yl]-1H-pyrrolo[2,3-
b]pyridin-3-yl]-5-methyl-thiazole
E132
2-[4-[(5R)-2,6-diazaspiro[4.5]decan-2-yl]-1H-pyrrolo[2,3-
b]pyridin-3-yl]thiazole
E133
2-[4-[(5S)-2,6-diazaspiro[4.5]decan-2-yl]-1H-pyrrolo[2,3-
b]pyridin-3-yl]thiazole
E134
2-[4-[(5S)-1,7-diazaspiro[4.4]nonan-7-yl]-1H-pyrrolo[2,3-
b]pyridin-3-yl]thiazole
E135
2-[4-[(5R)-1,7-diazaspiro[4.4]nonan-7-yl]-1H-pyrrolo[2,3-
b]pyridin-3-yl]thiazole
E136
3-[4-(1,7-diazaspiro[4.4]nonan-7-yl)-1H-pyrrolo[2,3-b]pyridin-
3-yl]isothiazole
E137
4-(1,7-diazaspiro[4.4]nonan-7-yl)-3-(2-pyridyl)-1H-pyrrolo[2,3-
b]pyridine
E138
8-[3-(2-pyridyl)-1H-pyrrolo[2,3,b]pyridin-4-yl]-1,8-
diazaspiro[5.5]undecane
E139
(6S)-8-[3-(2-pyridyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1,8-
diazaspiro[5.5]undecane
E140
(6R)-8-[3-(2-pyridyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1,8-
diazaspiro[5.5]undecane
E141
2-[3-(2-pyridyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-2,6-
diazaspiro[4.5]decane
E142
3-[4-(1,8-diazaspiro[5.5]undecan-8-yl)-1H-pyrrolo[2,3-b]pyridin-
3-yl]-4-methyl-isothiazole
E143
2-[4-(1,9-diazaspiro[4.5]decan-9-yl)-1H-pyrrolo[2,3-b]pyridin-3-
yl]-5-methyl-thiazole
E144
2-[4-(2,6-diazaspiro[4.5]decan-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-
yl]-5-methyl-thiazole
E146
2-[4-[(6S)-1,8-diazaspiro[5.5]undecan-8-yl]-1H-pyrrolo[2,3-
b]pyridin-3-yl]-5-methyl-thiazole
E147
2-[4-(1,8-diazaspiro[5.5]undecan-8-yl)-1H-pyrrolo[2,3-b]pyridin-3-
yl]-5-methyl-thiazole
E148
2-[4-[(6R)-1,8-diazaspiro[5.5]undecan-8-yl]-1H-pyrrolo[2,3-
b]pyridin-3-yl]-5-methyl-thiazole
E149
2-[4-(1,8-diazaspiro[5.5]undecan-8-yl)-1H-pyrrolo[2,3-b]pyridin-3-
yl]thiazole
E150
2-[4-[(6S)-1,8-diazaspiro[5.5]undecan-8-yl]-1H-pyrrolo[2,3-
b]pyridin-3-yl]thiazole
E151
2-[4-[(6R)-1,8-diazaspiro[5.5]undecan-8-yl]-1H-pyrrolo[2,3-
b]pyridin-3-yl]thiazole
E152
2-[4-(1,7-diazaspiro[3.4]octan-7-yl)-1H-pyrrolo[2,3-b]pyridin-3-
yl]-5-methyl-thiazole
E153
2-[4-(1,8-diazaspiro[3.5]nonan-8-yl)-1H-pyrrolo[2,3-b]pyridin-3-
yl]-5-methyl-thiazole
E154
2-[4-(1,7-diazaspiro[4.4]nonan-7-yl)-1H-pyrrolo[2,3-b]pyridin-3-
yl]thiazole
E155
2-[4-(2,6-diazaspiro[4.5]decan-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-
yl]thiazole
E156
4-(2,6-diazaspiro[3.5]nonan-6-yl)-3-pyridazin-4-yl-1H-pyrrolo[2,3-
b]pyridine
E157
8-(3-pyrimidin-2-yl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1,8-
diazaspiro[5.5]undecane
E158
2-[4-(1,8-diazaspiro[5.5]undecan-8-yl)-1H-pyrrolo[2,3-b]pyridin-3-
yl]-4-methyl-thiazole
E159
4-[4-(1,8-diazaspiro[5.5]undecan-8-yl)-1H-pyrrolo[2,3-b]pyridin-3-
yl]-2-methyl-thiazole
E160
8-[3-(2-methylpyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1,8-
diazaspiro[5.5]undecane
E161
4-(1,7-diazaspiro[4.4]nonan-7-yl)-3-pyridazin-4-yl-1H-pyrrolo[2,3-
b]pyridine
E162
2-(3-pyridazin-4-yl-1H-pyrrolo[2,3-b]pyridin-4-yl)-2,6-
diazaspiro[4.5]decane
E163
7-(3-pyridazin-4-yl-1H-pyrrolo[2,3-b]pyridin-4-yl)-2,7-
diazaspiro[4.5]decane
E164
4-(2,7-diazaspiro[4.4]nonan-2-yl)-3-pyridazin-4-yl-1H-pyrrolo[2,3-
b]pyridine
E166
8-[3-(2-methylpyrimidin-5-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1,8-
diazaspiro[5.5]undecane
E167
4-[4-(1,8-diazaspiro[5.5]undecan-8-yl)-1H-pyrrolo[2,3-b]pyridin-3-
yl]-3,5-dimethyl-isoxazole
E168
8-(3-pyrimidin-4-yl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1,8-
diazaspiro[5.5]undecane
E169
8-[3-(3-fluoro-2-pyridyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1,8-
diazaspiro[5.5]undecane
E170
8-[3-(5-fluoro-2-pyridyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1,8-
diazaspiro[5.5]undecane
E171
8-[3-(5-fluoro-3-pyridyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1,8-
diazaspiro[5.5]undecane
E172
8-(3-pyridazin-4-yl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1,8-
diazaspiro[5.5]undecane
E173
(6R)-8-(3-pyridazin-4-yl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1,8-
diazaspiro[5.5]undecane
E174
(6S)-8-(3-pyridazin-4-yl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1,8-
diazaspiro[5.5]undecane
E175
8-(3-pyridazin-3-yl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1,8-
diazaspiro[5.5]undecane
E176
3-methyl-1-(3-thiazol-2-yl-1H-pyrrolo[2,3-b]pyridin-4-yl)-
piperidin-3-amine
E177
3-ethyl-1-[3-(5-methylthiazol-2-yl)-1H-pyrrolo[2,3-b]pyridin-4-
yl]piperidin-3-amine
E178
3-methyl-1-(3-pyrimidin-5-yl-1H-pyrrolo[2,3-b]pyridin-4-
yl)-piperidin-3-amine
E188
8-[3-(1-methylpyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1,8-
diazaspiro[5.5]undecane
E189
8-(3-pyrazin-2-yl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1,8-
diazaspiro[5.5]undecane
E191
2-(3-pyrimidin-5-yl-1H-pyrrolo[2,3-b]pyridin-4-yl)-2,8-
diazaspiro[4.5]decane
E192
(6R)-8-(3-pyrimidin-5-yl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1,8-
diazaspiro[5.5]undecane
E194
2-(3-pyrimidin-5-yl-1H-pyrrolo[2,3-b]pyridin-4-yl)-2,8-
diazaspiro[5.5]undecane
E195
9-(3-pyrimidin-5-yl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1,9-
diazaspiro[4.5]decane
E196
8-(3-pyrimidin-5-yl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1,8-
diazaspiro[5.5]undecane
E206
(6S)-1-methyl-8-(3-pyrimidin-4-yl-1H-pyrrolo[2,3-b]pyridin-4-
yl)-1,8-diazaspiro[5.5]undecane
E207
(6S)-1-ethyl-8-(3-pyrimidin-4-yl-1H-pyrrolo[2,3-b]pyridin-4-
yl)-1,8-diazaspiro[5.5]undecane
E208
(6R)-1-ethyl-8-(3-pyrimidin-5-yl-1H-pyrrolo[2,3-b]pyridin-4-
yl)-1,8-diazaspiro[5.5]undecane
E209
2-[4-(1-ethyl-1,8-diazaspiro[5.5]undecan-8-yl)-1H-pyrrolo[2,3-
b]pyridin-3-yl]thiazole
E210
2-[4-(1-ethyl-1,8-diazaspiro[5.5]undecan-8-yl)-1H-pyrrolo[2,3-
b]pyridin-3-yl]-5-methyl-thiazole
E236
3-[4-[1,8-diazaspiro[5.5]undecan-8-yl]-1H-pyrrolo[2,3-b]pyridin-3-
yl]-1,2,4-thiadiazole
E237
2-[4-(1,7-diazaspiro[4.4]nonan-7-yl)-1H-pyrrolo[2,3-b]pyridin-3-
yl]-5-methyl-thiazole.
13. A pharmaceutical composition which comprises a compound according to claim 1 , or a pharmaceutically acceptable salt or solvate thereof, and one or more pharmaceutically acceptable excipients.
14. A combination comprising a compound according to claim 1 , or a pharmaceutically acceptable salt or solvate thereof.
15. The compound of claim 1 , or a salt, hydrate or solvate thereof, selected from:
Structure
IUPAC Name
E116
3-[4-[(6S)-1,8-diazaspiro[5.5]undecan-8-yl]- 1H-pyrrolo[2,3-b]pyridin-3-yl]-1,2,4-thiadiazole
E120
3-[4-[(6S)-1,8-diazaspiro[5.5]undecan-8-yl]- 1H-pyrrolo[2,3-b]pyridin-3-yl]isothiazole
E117
(6S)-8-(3-pyrimidin-4-yl-1H-pyrrolo[2,3- b]pyridin-4-yl)-1,8-diazaspiro[5.5]undecane
E150
2-[4-[(6S)-1,8-diazaspiro[5.5]undecan-8-yl]- 1H-pyrrolo[2,3-b]pyridin-3-yl]thiazole
E174
(6S)-8-(3-pyridazin-4-yl-1H-pyrrolo[2,3- b]pyridin-4-yl)-1,8-diazaspiro[5.5]undecane
E206
(6S)-1-methyl-8-(3-pyrimidin-4-yl-1H- pyrrolo[2,3-b]pyridin-4-yl)-1,8- diazaspiro[5.5]undecane
E133
2-[4-[(5S)-2,6-diazaspiro[4.5]decan-2-yl]-1H- pyrrolo[2,3-b]pyridin-3-yl]thiazole
E209
2-[4-(1-ethyl-1,8-diazaspiro[5.5]undecan-8-yl)- 1H-pyrrolo[2,3-b]pyridin-3-yl]thiazole
E139
(6S)-8-[3-(2-pyridyl)-1H-pyrrolo[2,3-b]pyridin- 4-yl]-1,8-diazaspiro[5.5]undecane
E207
(6S)-1-ethyl-8-(3-pyrimidin-4-yl-1H- pyrrolo[2,3-b]pyridin-4-yl)-1,8- diazaspiro[5.5]undecane
E146
2-[4-[(6S)-1,8-diazaspiro[5.5]undecan-8-yl]- 1H-pyrrolo[2,3-b]pyridin-3-yl]-5-methyl- thiazole
E126
(5S)-2-(3-pyrimidin-5-yl-1H-pyrrolo[2,3- b]pyridin-4-yl)-2,6-diazaspiro[4.5]decane
E131
2-[4-[(5S)-2,6-diazaspiro[4.5]decan-2-yl]-1H- pyrrolo[2,3-b]pyridin-3-yl]-5-methyl-thiazole
E210
2-[4-(1-ethyl-1,8-diazaspiro[5.5]undecan-8-yl)- 1H-pyrrolo[2,3-b]pyridin-3-yl]-5-methyl- thiazole
E171
8-[3-(5-fluoro-3-pyridyl)-1H-pyrrolo[2,3- b]pyridin-4-yl]-1,8-diazaspiro[5.5]undecane
E168
8-(3-pyrimidin-4-yl-1H-pyrrolo[2,3-b]pyridin-4- yl)-1,8-diazaspiro[5.5]undecane
E128
(5S)-2-(3-pyrimidin-4-yl-1H-pyrrolo[2,3- b]pyridin-4-yl)-2,6-diazaspiro[4.5]decane
E114
4-[4-(1,8-diazaspiro[5.5]undecan-8-yl)-1H- pyrrolo[2,3-b]pyridin-3-yl]isothiazole
E155
2-[4-(2,6-diazaspiro[4.5]decan-2-yl)-1H- pyrrolo[2,3-b]pyridin-3-yl]thiazole
E236
3-[4-[1,8-diazaspiro[5.5]undecan-8-yl]-1H- pyrrolo[2,3-b]pyridin-3-yl]-1,2,4-thiadiazole
E176
3-methyl-1-(3-thiazol-2-yl-1H-pyrrolo[2,3- b]pyridin-4-yl)piperidin-3-amine
E170
8-[3-(5-fluoro-2-pyridyl)-1H-pyrrolo[2,3- b]pyridin-4-yl]-1,8-diazaspiro[5.5]undecane
E169
8-[3-(3-fluoro-2-pyridyl)-1H-pyrrolo[2,3- b]pyridin-4-yl]-1,8-diazaspiro[5.5]undecane
E136
3-[4-(1,7-diazaspiro[4.4]nonan-7-yl)-1H- pyrrolo[2,3-b]pyridin-3-yl]isothiazole
E178
3-methyl-1-(3-pyrimidin-5-yl-1H-pyrrolo[2,3- b]pyridin-4-yl)piperidin-3-amine
E142
3-[4-(1,8-diazaspiro[5.5]undecan-8-yl)-1H- pyrrolo[2,3-b]pyridin-3-yl]-4-methyl-isothiazole
E129
3-[4-(2,6-diazaspiro[4.5]decan-2-yl)-1H- pyrrolo[2,3-b]pyridin-3-yl]-1,2,4-thiadiazole
E134
2-[4-[(5S)-1,7-diazaspiro[4.4]nonan-7-yl]-1H- pyrrolo[2,3-b]pyridin-3-yl]thiazole
E122
(6S)-8-(3-pyrimidin-5-yl-1H-pyrrolo[2,3- b]pyridin-4-yl)-1,8-diazaspiro[5.5]undecane.Cited by (0)
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